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The document discusses haloalkanes and haloprenes, including their classifications, properties, and reactions. It covers preparation methods from hydrocarbons, nucleophilic substitution reactions, and the physical properties of haloalkanes. Key points include the behavior of halogens, the impact of molecular size on boiling points, and the mechanisms of reactions involving haloalkanes.
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Save Haloalkanes and Haloarenes notes For Later HALOALKANES & HALOpRENES--_
RES RSENES
Akkanes > y phate _ | ia
Awe = ttt aber CM
__| App) ications:
| Sebvents = New - potas: tempos een
cL
ee st ae
eee
Bee rao Aube Htsiz Lei
panisiabives of alleen as
Cry Honto
Po cnn eng Cost =
R— Ahh’
olan ali tla Ld
2 Bored on Go 24 HatYe
corte all have 2 hydrogen ators aSledad
ily ttn catber 4
Beet SCH ec Namen
See ee Peresiceal)
| 2°
*_enben Ahmiid have | hud. abtachod Br:
* 2 tanben atoms
Ay, io. ei I
CH, — cH — x R— eit —x [ey
3,
ae
3
— CH,
ae CHa.
Ses
|
Soa .
aa
ee —
i abo seo BE NZYLIG HBL DES! abs pie te ts ar
—]—_ 9p is Colled__hengaphic tae eee
.
e
2
epee
&
pee ie ag
| > Benzene Suing Uthon _aktarhed te CHa psu s
ce
ae Ce Hs =p = Pa
CeHp=Cap- Ue
Aoi pi pes eee
' ate
> CHa = CH =a) = xe
Fagg om Ea
« ies aited te a Carib a?
| deuble re i
tralidos .
By: (Goes CH, = CH= Boe Te
Gi =U, —H, —. ee
i ee|
|
Se ae
ce. OH
—___ | Alieyetic warines: I |. Us butane
aa,
—| ten tne hy drogen. aaa aye butane Js
| steplaced by Deer habogey ——eP
eee a se
VINYI HALIDES”
CHa = ch— Xx
So igs CH=
[Halagen acing thle 2_sp—hypaatsisel
dim. of a conben— tonben daulale |—-— mnie
ee
erasa
Pay jPRePanatowhecakbaubiaeANieg./ os
| Brees,
ete) Cs ee aa aE Danyon’s arn)
a) tenecarbens 2 si Bh
FROM AL CoHoLS :
=97 i
ReOncE SS = haloalkanss
: 1X
il) Phesphosus halides _Pxg 0 Px
fil) Thiewf. Wheride
Roastim rh Festal with hyde gen holides :
° 9 3° Caburhok)
cs [a ENB ete Ae
HE, HO, Heo WE halides)
fen aluoho, 3° ¥ 2° > 1° ®
Hoy 1695 H HE Cro noun,
UE xa all
Gn b.Alurnts wath Hs ee
oo sud th 1° aheotot _onby man
a_cokolynt 2° ale : Va
| Gtalyst > Andy Ares Zoihy + on -H OL => Laced suse
anh Zn tls é
CH, HH. OH + HU => cH ce +40
alone € +h one
H_tembines with pt 40 fern HO
OW neplorcod by ce ‘
Only ay :
! = Sinky: Zn la +o
CH, = C= tHU —— > ch, -¢- + H,9 a
t ! e
ou = a
Q-ererpoepen a a
ety ie —&
“Sal See SMO cedeces 2t-4 + He0
=
CH3. £99 =
Q-chlane am ety e — =
os eo
x
——"
es
. sl rr el 4 3
SS =
SS eee
ae a wsAtehals with HBr: are
Q@_48 °/o HE Cumstart bo! fag rf alichet )
Be RAE SO ibis hs eater ito
ot = Cay ba + H20+ KHS04
SP iis Nar. cd kD in 5i15P04 (erthe phophevic aid)
whould net we Ha$04 because uk oridlision
Min stk, jon ade
nce wont get dori
© si 2fe wer fee
___| Reactions of aletiats mith i —Phasp hosus halides: :
Chet planus holids + PX. (oy BX,
ce P Che PCes
od P+ Bou PB. ase m site.
race | a Ate 3
Red P+ Ta] I f13 : !
Se aa oy
= ¥ +Ppa sh Hu + POUs ___-
hts a
ei ie
+ aa 2.
__ 4 Ti
peas pig eeSanger! si
— Reketiont a aber tan Riengl ae
pyridine
agmation:CHy CH, OH + Sod, > cn, Hach + SO nm
| + This seattion is pe aca ta en
| _moactiens because both +t
(eciare ate _
+ S0B4,) > unstable i
Sot, dees net mist X
| PREPARATION of HALOALKANES fran HYDROCARBONS:
ee
Foupanation Apron. alkanes! ge :
Grontrod — Apdmua. + Cy Hays 4H + —
R= x XK Fd) Ba, oc
fee
ee a FaF voy ee
spuuninse on abkone ene rest give vor | hgh, —
i...
> Therehons wit used, ill :HI
i
blenina tion = $e Baumutna bene Atha eutetme um)
Lakes plows si proson en UV Meme oh hot
ere ene
é < are ame Systeny
Cis + a, “> CHa + no
pt Carter me thane.
eo. CH, As, —» cha, He
tS
Ak-chlere methane
Leda 4 aeiee Hp
~ ott CH, @, 4c, => CHC + Hee
speqttbeshis® “she qungonsina ns ye chhae
methane
CHU, +, — CCtg + Hd
es es otc Canbon Hela chlatile —__
nvReaubiuity anton in Heong:
! Ber y iy Ue =o
SS onder uh th allogens:
— oo
i C an, Beene: ere
hk
5 = [- Chloow psropana A-chierep nepand
\ Ayer es 7-2
Ae Q - Soop
~ i =
tte agen halides + HE, Hot, HB2- HE
Aahournaune =
—
——|—__Ct = a, + - x —> cu, - —_+ > Yrs nb with mat
(Hetsg)) — > jes cortbore wilt feast “hy dolage
Reaction: with aymmetaic alkenes assis
Cpe Sed ap eyres Cy CH = CH
|
—— Fy —Markeynitver’ rule; ZT imams
The Hin H- nee eee
Ploegh talved init dauble end dais
=) » dt hes 2 possibilities bub it deine
With the eare double -bendad canben which hes
——| mre hy dlaco gen ates die, Cha — CH =@2)
5 s le — bond ts Siu
Hh _siemoved: APES siniy g _
abe gen jponins ul Hh mid _tnben hane / HW deficient —
Corben .
saat jin on oven oe ane sad of, paresis
—— lta eaping — Avi Mankvnilenrusla. — 2a His
See ee ep
Sma R anes
| Aeomar and halogens * ——
[= G1, + By =. “fy = Sus
eee | SE ees eee:
IE
SS Bn Ba -
Mieinal di = Bowmiole __ 5
rac pee ahem op dele tt
—__| - Sm poaitavek mat 4
Bee tata Ben oh Devenish fn a
prea or y[PREPARATION OF HPLOALKANES | nN era
| ——___EXCHAna.e REACTIONS. _ S
* Preparation. eh Jode-= ‘ Propanatiin of Fluere-
Atkancs er _ableyl iodidas alkanes or af kyl fluo si dos
af Nak in dry atetme Ag, SbFs.Hgaf,
saGor
+ PikyR Unlerida 0% a Ak ky _chlaride or
OdkeyR prvernide allyk bromide
a4 STEIN 3 ee a Wer
1CH3Ch, Bot Na abst CH, 2D _
; ore tone Joda ethane
EHaCHaBn + Age => Cause + Ag Bn
-flusree Aey)
—-PRNS ICA L-PROPERTIES oF HALOALKANES:
1) Lote i ie
Gees Pino holdalkanes? <5. Urlewlors
BES Boternballkomes te eee ed
Jo deatkounos Aight ? erteunad
2) Sheil?
KVetatile Sralogtn tompeurds have guise small _
3) « Haloatkones with Phuysleal state :
Ly Rh _3_C sre _gares at new T
Atenrd
£5 Cig co, CHy Bn, Co He Bm
%_Hateolieanes with
3B. Cates are higutds or solids
4) Melting and Boiling Pinta:fu,
| ge uton Cempaned t® then parent alkanes, 4 i
_\ ove — Fria hres | bosbiy point: 2 and ee ao
RLY RBn Ray RE eS
seeps big 8132 Bde doula has one Nigtal
$ Vondeswaols -bonce is high BP %
BP X size of motewleg
Bip Mokoustan mares
Beep 1 Vandaruuools fee =
Bp XL ne-ef halogen atoms.
ty: COly > CHU, > CHAM, D CHy ce
E Chg udo Ty CH Ula Bnd Cty Hy U7 Cy cE ——
ae ain Motes abkaring
ia! pie aoe inp =o apes
foes — ——
i.
docneares Cbeerme wort)
Bip oe ! =
$$$ Bonn iy lee Sa =
we
— ut act cH ae ae
wt <Se
@ Ps
Pan wy
= ee Onno meta ise
Reasen Shy mmising of ot, pace ds a ee
MONA — lala _Cpiaatt 10 break’)
Be) SoRulei lity «
dg
“Halealk anos Ore Very Sighs on ss ae
£ They _cannet farm tk bends wit wudlen .
| een actions by pal
PE ae have tonsidorable Atacng te
6) analy
Bea Sear Rd pple teal tipo ome
[ous Deni = oli nna of “corpo dors SS
oe ol poe haley outa
Jke Maren! Nucloophilic Subshtution saactior
pee sein suacti ons Voa
S Reaction with metals
NOCLEOPHILIC. SUBSTITUTION REACTIONS wiv a
HALOALKANES + e =
R-X
+ =
rae x& =
LL These reactions take pla betause. ct. enae Separiatiory
iy |
ec ae —. x q
ee Nu 2
Ne 5
ae has Change $0 Jk us attacked by an A
pi leophle A
= C-K Bubstoste a
bh S i Nu Inerning oe a
: x dansing POP
~o*#—_4- s
Net =C = > Nu Cue x 3
: 3
=
Aulssto
gent ltt a haledlkang dawg
Yeehange ft om ¢ atore.
LAAAAABAESTES
K | Qn. (% os)
Holealkanes rence with KON ite etm aku tyanides
while AGCN _ germ& Jromanides Explain
Ken AgtN :
__| Chath fans Bien => CHO, CN + KBox
oo fests cH, fas Aden Pests Lata tg Ba
= Neda) Jee Simagentes ss cui NSCS Re
KON. uenic Kt cN nee
Ag cn. covalent N connected wocganide
NO.” N-linked oh O= linked4
Be SEPMECHANISM (2
=e = ad
eee af
Swine
alia Lowe ae
:
SN 7 a,
Cee A :
a” x = ese = tk :
t
F é
X_ Senyes ond then Nu attacks =So,1 6
X_leaves ok the Same time Nu” = ono :
_CSimultansond) ortac ks «
‘
«
8
2
= Inueming Nuteephile must be STRONG NUCLEO ¢
ds = PHLE ‘i
The ntering mucdeephile idtarads uit abby? halide :
————
ee (ee bond to break and a noe
C and Nu ____—_-¥
%
Sy bendvvo rans pla
oNtasail. Ram ee bon teug of a
maodvote 43 ii 220
ee *
aMee teppei here 2
|= He suattion presumes:
Bond bohiveon incom . es yi
| _ atm stant yonirg.? muclaspdisse and, carbon
Soe Bond betwen carbon aim. and nui group
—} 8624 bends vp the atbetrates tralealhonad)
gee | Abas —mauing omcy fram attacking huveleep hile
SANE ree bree ges
till keop_tnowing in_seme dérwctor
| _A_ oe 3) Nuchepbille attornes uit carbon
ee ign e ines te cle
Bt | 5 a sasutt Configuration of anben atom
vs inverted by 4 panncans — Jinversion Of. configuration
2. =| PRAGMA RROMAMEW! 8 ne
ao =H ae: Ae
OH a fiber Sf Sc
H
Cinultonoons| Wy bended
5 ahennt
Cp darenee = Pile, ak ules Hituenct en eo) naan Cater
Onder of, Reach. wity Wes an efpet on nu) .
[etigt 9 Tae a
[Rory e- gues am >> R-F
E-SNa svc ANGE Mi ieee Sel ale
| SN, > Nuckeopdilic Substitution wrimofeudar:
tet of "Fae stan wines eoeetaes of
_dvottte =
|
Add dpe ala a ‘miatatass a8
PA pp
| Reardon et in case pc —__—__—
Se onl Lae | (only a)Step i:
2 The potas ¢- X bond wag show
ee aoe)
Analide”
Cue
se DS 12
(CH3), Cen glow Cts Ory
Step 2
> The cnboustion thus ormad. ws Han athaseed
creothion
|
Be Pepe CC), Cou
Crt >
| Mechoutsm. +
= Step Tis rho and rersible
t nat C= & band er
¥ > Cinergy for _borwsaleng bonold Ja ebtated threugh| =2 Gureaten the stalsili of, dasa tates ea
| _Ganeaker with be its” ane of famatter,
pat ety halide So
Faster ull be tte suite of, 0 el rn
Onder of Reade uity :
as gt]
STEREOCHEMICAL ASPECTS of NucLeopHitic sosstiTTssal a is
Plann eh plone peoditubad 0 ight _priodustd by
=} — potas, —wingtaniand fondihatiy Hig hd: Hirer NM tert
usm "us suototd when pared 4
tantadny
—___| com pounds Bde ee tadpole as
ia _awaile. | ote ae ee
| gretaled ws
Colled _petasimatar
> Compound maker the prlanined Light to stale
an jgtce yea called. dackosuttatony d—petm.
(4D
> Compound oakos fe polarised Night cfe_natelt
He Robe, ik ia tolled oovontadssy » f= fpr —
&
> Seeman 2h 0 tompnuid ust pa
ia pt vpficegl daamant_annch —
a eh icles sy(ey
[ip auetaadans asymm 2
=> Feun Greups around the catia, sdoloee ee in
—diirohedrat Od ip all substi tucks atlarhed. to
Corben are diPos and 4 the manner, imago
ih the melee i net Aupen cimpesable ery the —
| —_mrbrule . Such a Gaben us cabled asymmifede _
—|—_tanbery 0) Shoronetro
il) inabity. ;
2 The imetetubos hich oro net! Aupercimpesable —
om thei mio Image ane Caled chuial mofewles| Otten —_oramp ler of utah metoutar !
a =Unlorebitane » 2,3- di ydneny propanall
| brome chilere -iodemethano » &— brome propaneic oud.
| eae ee nee at err
Aupor-impesale Imire Images axe called enaxtomars
2 Adentical ob) melting eoirt
Tra,
/
|
A ea
“¢ CH 3 ee shire 5
| 24mg +oh +HU —> He ee
i, oblie e
| ee lara e
eee
ee NG
eee
= a a
© : :
£
Reasemisation: Se*/o ef invensivn pnodut =
-e
Se OP aotenhinn cpeded —
DRoumuation product
poopSh
ji Reverie miidine wh a wibttine uh:
50 °/o (+) form _Ond Bo*le (=) porwr